A few years ago, in 2016, H. Moser sprung one of its trademark surprises. A tiny indie manufacturer, with no previous history of working with celebrities, let alone bona fide legends of the music biz, announced that it had co-designed a watch with Mr Bryan Ferry. It wasn’t much like the H. Moser watches of today – it sat in its “heritage” line, a gold-cased, white-dialled exercise in restraint, the only nod to the partnership being the words “Bryan Ferry” where it would normally say “Swiss Made”. All of which is to say when it comes to sharp, understated, classy wristwear, Ferry has form. Here he is – exuding dominance in a white tuxedo – wearing a gold Boucheron Reflet (a lesser-known dress watch in the mould of a Tank or Reverso, first launched in 1947) that unfortunately went missing some years later, as he told the Telegraph in 2016. “It was beautiful, like a Cartier Tank. I occasionally spot it in archive shots…”

Where to start? Perhaps the fact that in every single picture of Jay-Z, the hip-hop superstar has a different – and exquisite – watch. He wore a Patek Philippe Grand Master Chime, a $2.2m inner-circle-only hall-of-fame watch, to Diddy’s birthday party. He has collaborated with both Audemars Piguet and Hublot on his very own limited-edition designs. His tastes extend far beyond any cliché of his industry; there may be gold and there may be diamonds, but there is depth and subtlety to match. Case in point: this courtside shot from 2016, where he sports a Jaeger-LeCoultre Reverso Tribute in rose gold. We’re always talking about dressing down the Reverso – this is how it’s done.

Mr Ed Sheeran isn’t flash. You won’t see him drinking buckets of champagne in a Miami nightclub or bustling past paparazzi into a tinted Rolls-Royce. But he might just have one of the most enviable watch collections in the world. It can escape your notice when the hair, the T-shirt and jeans haven’t changed since his days as an itinerant busker, but without fail, Sheeran’s wrist is home to a hard-to-get Patek Philippe, Rolex or occasionally some other idol of true watch-geek status. Pictured here at Glastonbury in 2014, for example, Sheeran is wearing a Patek Philippe 5270 in white gold: that’s a perpetual calendar chronograph, arguably the brand’s signature complication, and an absolute masterpiece of high-end watchmaking that, no joke, every single watch collector on the planet would want to own. But here it is at Glastonbury festival. Truly, the man’s no-fucks-given approach demands respect.

Reportedly, Mr Lionel Richie only came on board for Live Aid – shown here performing at JFK Stadium in Philadelphia on that hot July day – at the last minute. But what could be more 1980s than Richie at the absolute height of his fame (between 1983 and 1986 he had eight top 10 singles and two number one albums), performing alongside Mr Michael Jackson no less? And what could be more 1980s than this look: cream pinstripe suit, sleeves rolled up and shoulders you could land a helicopter on? The piece de resistance of any 1980s power dressing, however, had to be a gold Rolex. Richie’s watch is a little bit hard to identify – we’re pretty sure it’s a Datejust 6824 or Oyster Perpetual 31mm, but could at a pinch be a 160xx series Datejust 36mm. What’s certain is that it’s a mid-size Rolex with an 18k yellow-gold Oyster bracelet and case with champagne-gold dial. He wears it loose – of course he does. The lesson for today’s collector? Nothing wrong with a smaller diameter, especially if it’s got the weight of gold behind it.

“Check out my diamonds, bitch/Everyone gon’ blink” Mr Tupac Shakur so memorably intoned on, ahem, “Fuck Friendz”, from his third posthumously released album Until The End of Time. Tupac loved his diamond-set Rolexes so much that he was frequently seen wearing one on each wrist, alongside a number of rings, chains and bracelets. Photographed here in Harlem in 1993, the watch stands out against his otherwise featureless outfit. It’s almost certainly the first customised Rolex he bought, and although all things are relative, is less ostentatious than some that would follow. An 18k yellow-gold Day-Date with a diamond-set bezel and diamond hour markers, it has erroneously been described as a rare pyramid reference, but nevertheless it is a classic choice: the OG of rap watches. Which is pretty much exactly what you would expect.

It can seem, sometimes, like there’s nothing Mr Mark Ronson can’t turn his hand to; he has that knack of bringing disparate voices and influences together and moulding them into something destined for mainstream appeal. There’s really only one watch brand for the multi-hyphenate super-collaborator: Audemars Piguet. A true heavyweight with unimpeachable technical skill and a long history, since 2000 it has also worked with more entertainment galacticos than pretty much any other watchmaker. You might expect Ronson to rock a Royal Oak Offshore – the calling card of many a musician – but his personal style hews far more closely to the all-time classics. It has to be a Royal Oak; a reference 5402BA, to be specific. This yellow-gold Jumbo was produced from 1977 into the early 1980s (later versions have the AP logo at six, which doesn’t appear on Ronson’s watch) and is highly sought-after today.

One of the nice things about charting the history of musicians and watches is realising that it goes back far beyond the modern era of official partnerships and collaborations. Mr Harry Belafonte, Mr Frank Sinatra and Elvis all loved a good watch. Same goes for the jazz legends: Mr Miles Davis’s Navitimer is pretty well documented, but how about Mr Duke Ellington’s Cartier Tank? This is an offbeat watch for an offbeat world – the rare, incredible Tank à Guichets. Guichet translates roughly as “window” or “aperture” – as you can see from the watch, its signature feature is that the dial is replaced by a solid steel front, with openings through which the hour and minutes can be read. It’s a wonderful piece of 1930s watchmaking, and a good match for Ellington’s immaculate double-breasted suit; a touch of eccentricity within a finely tailored look.

If you only know Bad Bunny as a funny name – or perhaps not at all – allow us to fill you in. The genre-melting Puerto Rican rapper and singer got his break in 2016, but really attained all-conquering status last year, performing at the Superbowl half-time show, releasing the first Spanish-language album to top the Billboard 200, and ending the year as Spotify’s most-streamed artist. One of his songs was even used by President Joe Biden in a presidential campaign ad. So it’s fair to say he could have his pick of fancy wristwatch. Pictured here performing at Rihanna’s Savage X Fenty Vol.2 fashion show, he’s not wearing a blinged-out Jacob & Co monster but a Cartier Ballon Bleu. There’s something reassuring in the consistency and breadth of Cartier’s appeal, from the Duke to Bad Bunny. Classic design never goes out of fashion, as they say.

The man, the meme, the legend: Drake’s rise to hip-hop’s top table over the last decade has been nothing short of stellar, and along the way he has amassed a watch collection to match. GQ called it the world’s most impressive watch collection. We won’t quite go that far, but it’s fair to say Drake is well and truly hooked. He has a particular fondness for Richard Mille (earlier this year he bought the $1.05m Rafael Nadal limited-edition RM 27-04, one of 50 models created especially for the tennis star), and if we’re honest, it suits him down to the ground. Pictured here courtside for the 2019 NBA playoffs between the Philadelphia 76ers and the Toronto Raptors, it’s hard to miss the RM 11-03 flyback chronograph, custom-set with diamonds on every surface of the rose-gold case.

The country music star that’s not like other country musicians – he cites Run-DMC and the Beastie Boys as inspiration – is a serious and eclectic watch collector. Spotted in a whole host of brands – the Rolexes, Audemars Piguets and Patek Philippes aren’t a huge surprise, but he also owns a lot of less obvious watches, including models by Jacquet Droz and Chopard, and off-piste pieces from major brands such as IWC Schaffhausen’s Aquatimer 2000 or the Richard Mille RM 63-01 Dizzy Hands. Here, though, we’ve found possibly the most unlikely timepiece for a music megastar: the Breguet Tradition ref. 7047, a hugely complicated (and hugely delicate) creation that uses a tiny hand-made chain to meter out its power. Suffice to say it’s not something you’d associate with energetic on-stage performances, but Mr Bryan, we salute your connoisseurship.